Antitumor properties of tetrahydrobenz[a]anthraquinone derivatives.
The compound 8,11-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]- 6-methoxy-1,2,3,4-tetrahydro-7,12-benz[a]-anthraquinone (7) was synthesized from 3,6-dimethoxyphthalic anhydride and 6-methoxy-1,2,3,4-tetrahydronaphthalene by a Friedel-Crafts reaction, cyclization to form a dihydroxyanthraquinone, and conversion into the amino-substituted derivative by reaction with 2-[(2-hydroxyethyl)amino]ethylamine. The new compound, a ring D analogue of mitoxantrone, showed growth inhibition, at micromolar concentrations, of murine leukemia 1210, human lung H125, human breast MCF7, human ovary 121, and human colon WiDr and increased the life span of leukemic mice by 38%.
Morreal
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CE
Breast Cancer Research Unit, Roswell Park Memorial Institute, Buffalo, New York 14263.
Bernacki
R J
RJ
Hillman
M
M
Atwood
A
A
Cartonia
D
D
D000818:Animals; D000880:Anthraquinones / Q000138:chemical synthesis / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D055598:Chemical Phenomena; D002621:Chemistry; D004983:Ethanolamines / Q000138:chemical synthesis / Q000494:pharmacology*; D006801:Humans; D007939:Leukemia L1210 / Q000188:drug therapy; D051379:Mice; D008811:Mice, Inbred DBA; D008942:Mitoxantrone; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000880:Anthraquinones; D000970:Antineoplastic Agents; D004983:Ethanolamines; C062809:8,11-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-6-methoxy-1,2,3,4-tetrahydro-7,12-benz(a)anthraquinone; D008942:Mitoxantrone